MX9202287A - NEW DERIVATIVES OF PERHYDROISOINDOL, PROCEDURE FOR ITS PREPARATION AND PHARMACEUTICAL COMPOSITION THAT CONTAINS THEM. - Google Patents
NEW DERIVATIVES OF PERHYDROISOINDOL, PROCEDURE FOR ITS PREPARATION AND PHARMACEUTICAL COMPOSITION THAT CONTAINS THEM.Info
- Publication number
- MX9202287A MX9202287A MX9202287A MX9202287A MX9202287A MX 9202287 A MX9202287 A MX 9202287A MX 9202287 A MX9202287 A MX 9202287A MX 9202287 A MX9202287 A MX 9202287A MX 9202287 A MX9202287 A MX 9202287A
- Authority
- MX
- Mexico
- Prior art keywords
- halogen
- preparation
- perhydroisoindol
- procedure
- pharmaceutical composition
- Prior art date
Links
- ODSNARDHJFFSRH-UHFFFAOYSA-N 2,3,3a,4,5,6,7,7a-octahydro-1h-isoindole Chemical class C1CCCC2CNCC21 ODSNARDHJFFSRH-UHFFFAOYSA-N 0.000 title abstract 2
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 229910052736 halogen Inorganic materials 0.000 abstract 4
- 125000005843 halogen group Chemical group 0.000 abstract 3
- 150000002367 halogens Chemical class 0.000 abstract 2
- 150000003254 radicals Chemical class 0.000 abstract 2
- QDZOEBFLNHCSSF-PFFBOGFISA-N (2S)-2-[[(2R)-2-[[(2S)-1-[(2S)-6-amino-2-[[(2S)-1-[(2R)-2-amino-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]amino]hexanoyl]pyrrolidine-2-carbonyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-N-[(2R)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2S)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]pentanediamide Chemical compound C([C@@H](C(=O)N[C@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(N)=O)NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](N)CCCNC(N)=N)C1=CC=CC=C1 QDZOEBFLNHCSSF-PFFBOGFISA-N 0.000 abstract 1
- 102100024304 Protachykinin-1 Human genes 0.000 abstract 1
- 101800003906 Substance P Proteins 0.000 abstract 1
- 125000004442 acylamino group Chemical group 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000000278 alkyl amino alkyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000004103 aminoalkyl group Chemical group 0.000 abstract 1
- 239000005557 antagonist Substances 0.000 abstract 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 abstract 1
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- -1 phenyl radicals Chemical class 0.000 abstract 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Abstract
New perhydroisoindole derivatives of general formula (I) in which the radicals R are hydrogen atoms or together form a bond, the symbols R' are phenyl radicals which can be substituted by a halogen atom or a methyl radical in the 2 or 3 position, X is an oxygen atom or an NH radical, R1 is phenyl, which is optionally substituted, cyclohexadienyl, naphthyl or heterocyclyl, R2 is H, halogen, OH, alkyl, aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, alkyloxy, alkylthio, acyloxy, carboxy, optionally substituted alkyloxycarbonyl, benzyloxycarbonyl, amino or acylamino, R3 is halogen or OH and R4 is H or halogen if R3 is halogen, under their isomeric forms or their mixtures, optionally their salts when they exist and their preparation. The new derivatives according to the invention are particularly advantageous as antagonists of substance P. <IMAGE>
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9106035A FR2676442B1 (en) | 1991-05-17 | 1991-05-17 | NEW PERHYDROISOINDOLE DERIVATIVES, THEIR PREPARATION AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THEM. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MX9202287A true MX9202287A (en) | 1993-02-01 |
Family
ID=9412907
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX9202287A MX9202287A (en) | 1991-05-17 | 1992-05-15 | NEW DERIVATIVES OF PERHYDROISOINDOL, PROCEDURE FOR ITS PREPARATION AND PHARMACEUTICAL COMPOSITION THAT CONTAINS THEM. |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US5451601A (en) |
| EP (2) | EP0586490B1 (en) |
| JP (1) | JPH06507627A (en) |
| AT (1) | ATE135687T1 (en) |
| AU (1) | AU1883692A (en) |
| CA (1) | CA2109298A1 (en) |
| CZ (1) | CZ244793A3 (en) |
| DE (1) | DE69209290T2 (en) |
| DK (1) | DK0586490T3 (en) |
| ES (1) | ES2085627T3 (en) |
| FI (1) | FI935071A0 (en) |
| FR (1) | FR2676442B1 (en) |
| GR (1) | GR3019386T3 (en) |
| HU (1) | HUT67649A (en) |
| IE (1) | IE921578A1 (en) |
| IL (1) | IL101866A0 (en) |
| MX (1) | MX9202287A (en) |
| NO (1) | NO933964L (en) |
| NZ (1) | NZ242772A (en) |
| SK (1) | SK126793A3 (en) |
| TW (1) | TW200459B (en) |
| WO (1) | WO1992020653A1 (en) |
| ZA (1) | ZA923540B (en) |
Families Citing this family (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2689888B1 (en) * | 1992-04-10 | 1994-06-10 | Rhone Poulenc Rorer Sa | NOVEL PERHYDROISOINDOLE DERIVATIVES, THEIR PREPARATION AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THEM. |
| US5508424A (en) * | 1993-03-26 | 1996-04-16 | Ortho Pharmaceutical Corporation | 4-arylisoindole analgesics |
| FR2703679B1 (en) * | 1993-04-05 | 1995-06-23 | Rhone Poulenc Rorer Sa | NOVEL PERHYDROISOINDOLE DERIVATIVES, THEIR PREPARATION AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THEM. |
| FR2710913B1 (en) * | 1993-10-07 | 1995-11-24 | Rhone Poulenc Rorer Sa | New perhydroisoindole derivatives, their preparation and the pharmaceutical compositions containing them. |
| TW365603B (en) * | 1993-07-30 | 1999-08-01 | Rhone Poulenc Rorer Sa | Novel perhydroisoindole derivatives, their preparation and pharmaceutical compositions which contain them |
| FR2709752B1 (en) * | 1993-07-30 | 1995-10-06 | Rhone Poulenc Rorer Sa | New perhydroisoindole derivatives, their preparation and the pharmaceutical compositions containing them. |
| FR2710842B1 (en) * | 1993-10-07 | 1995-11-24 | Rhone Poulenc Rorer Sa | New therapeutic application of perhydroisoindole derivatives. |
| FR2719474B1 (en) | 1994-05-05 | 1996-05-31 | Oreal | Use of a substance P antagonist in a cosmetic composition and composition obtained. |
| US6203803B1 (en) | 1994-12-14 | 2001-03-20 | Societe L'oreal S.A. | Use of a substance P antagonist in a cosmetic composition, and the composition thus obtained |
| FR2719476B1 (en) * | 1994-05-05 | 1997-05-23 | Oreal | Use of a substance P antagonist in a cosmetic composition and composition obtained. |
| FR2727411B1 (en) * | 1994-11-30 | 1997-01-03 | Rhone Poulenc Rorer Sa | NOVEL PERHYDROISOINDOLE DERIVATIVES, THEIR PREPARATION AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THEM |
| FR2728165A1 (en) | 1994-12-19 | 1996-06-21 | Oreal | USE OF AN ANTAGONIST OF SUBSTANCE P FOR THE TREATMENT OF SKIN REDNESS OF NEUROGENIC ORIGIN |
| FR2728166A1 (en) | 1994-12-19 | 1996-06-21 | Oreal | TOPICAL COMPOSITION CONTAINING AN ANTAGONIST OF SUBSTANCE P |
| FR2728169A1 (en) | 1994-12-19 | 1996-06-21 | Oreal | USE OF A SUBSTANCE P ANTAGONIST FOR THE TREATMENT OF PRURITUS AND EYE OR PALPEBRAL DYSESTHESIA |
| FR2741262B1 (en) | 1995-11-20 | 1999-03-05 | Oreal | USE OF A TNF-ALPHA ANTAGONIST FOR THE TREATMENT OF CUTANEOUS REDNESS OF NEUROGENIC ORIGIN |
| DK1246806T3 (en) | 1999-11-03 | 2008-06-16 | Amr Technology Inc | Aryl and heteroaryl-substituted tetrahydroisoquinolines and their use in blocking the reuptake of norepinephrine, dopsmin and serotonin |
| US7163949B1 (en) | 1999-11-03 | 2007-01-16 | Amr Technology, Inc. | 4-phenyl substituted tetrahydroisoquinolines and use thereof |
| BR0112350A (en) | 2000-07-11 | 2003-06-24 | Albany Molecular Res Inc | Compound, pharmaceutical composition, and method of treating an animal afflicted with a neurological or psychological disorder |
| KR101412339B1 (en) | 2004-07-15 | 2014-06-25 | 알바니 몰레큘라 리써치, 인크. | Aryl- and heteroaryl-substituted tetrahydroisoquinolines and use thereof to block reuptake of norepinephrine, dopamine, and serotonin |
| US8362075B2 (en) | 2005-05-17 | 2013-01-29 | Merck Sharp & Dohme Corp. | Cyclohexyl sulphones for treatment of cancer |
| US7956050B2 (en) | 2005-07-15 | 2011-06-07 | Albany Molecular Research, Inc. | Aryl- and heteroaryl-substituted tetrahydrobenzazepines and use thereof to block reuptake of norepinephrine, dopamine, and serotonin |
| GB0603041D0 (en) | 2006-02-15 | 2006-03-29 | Angeletti P Ist Richerche Bio | Therapeutic compounds |
| US20110218176A1 (en) | 2006-11-01 | 2011-09-08 | Barbara Brooke Jennings-Spring | Compounds, methods, and treatments for abnormal signaling pathways for prenatal and postnatal development |
| PL2336120T3 (en) | 2007-01-10 | 2014-12-31 | Msd Italia Srl | Combinations containing amide substituted indazoles as poly(adp-ribose)polymerase (parp) inhibitors |
| CA2676357A1 (en) | 2007-01-24 | 2008-07-31 | Glaxo Group Limited | Pharmaceutical compositions comprising 3, 5-diamin0-6- (2, 3-dichl0phenyl) -l, 2, 4-triazine or r (-) -2, 4-diamino-5- (2, 3-dichlorophenyl) -6-fluoromethyl pyrimidine and an nk1 |
| CA2690191C (en) | 2007-06-27 | 2015-07-28 | Merck Sharp & Dohme Corp. | 4-carboxybenzylamino derivatives as histone deacetylase inhibitors |
| AR071997A1 (en) | 2008-06-04 | 2010-07-28 | Bristol Myers Squibb Co | CRYSTAL FORM OF 6 - ((4S) -2-METHYL-4- (2-NAFTIL) -1,2,3,4-TETRAHYDROISOQUINOLIN-7-IL) PIRIDAZIN-3-AMINA |
| US9156812B2 (en) | 2008-06-04 | 2015-10-13 | Bristol-Myers Squibb Company | Crystalline form of 6-[(4S)-2-methyl-4-(2-naphthyl)-1,2,3,4-tetrahydroisoquinolin-7-yl]pyridazin-3-amine |
| UA105182C2 (en) | 2008-07-03 | 2014-04-25 | Ньюрексон, Інк. | Benzoxazines, benzothiazines, and related compounds having nos inhibitory activity |
| WO2010114780A1 (en) | 2009-04-01 | 2010-10-07 | Merck Sharp & Dohme Corp. | Inhibitors of akt activity |
| US9034899B2 (en) | 2009-05-12 | 2015-05-19 | Albany Molecular Research, Inc. | Aryl, heteroaryl, and heterocycle substituted tetrahydroisoquinolines and use thereof |
| WO2010132487A1 (en) | 2009-05-12 | 2010-11-18 | Bristol-Myers Squibb Company | CRYSTALLINE FORMS OF (S)-7-([1,2,4]TRIAZOLO[1,5-a]PYRIDIN-6-YL)-4-(3,4-DICHLOROHPHENYL)-1,2,3,4-TETRAHYDROISOQUINOLINE AND USE THEREOF |
| KR101830447B1 (en) | 2009-05-12 | 2018-02-20 | 알바니 몰레큘라 리써치, 인크. | 7-([1,2,4]TRIAZOLO[1,5-α]PYRIDIN-6-YL)-4-(3,4-DICHLOROPHENYL)-1,2,3,4-TETRAHYDROISOQUINOLINE AND USE THEREOF |
| PE20121172A1 (en) | 2009-10-14 | 2012-09-05 | Merck Sharp & Dohme | PIPERIDINS SUBSTITUTED WITH ACTIVITY IN HDM2 |
| CA2805265A1 (en) | 2010-08-02 | 2012-02-09 | Merck Sharp & Dohme Corp. | Rna interference mediated inhibition of catenin (cadherin-associated protein), beta 1 (ctnnb1) gene expression using short interfering nucleic acid (sina) |
| CA2807307C (en) | 2010-08-17 | 2021-02-09 | Merck Sharp & Dohme Corp. | Rna interference mediated inhibition of hepatitis b virus (hbv) gene expression using short interfering nucleic acid (sina) |
| EP2608669B1 (en) | 2010-08-23 | 2016-06-22 | Merck Sharp & Dohme Corp. | NOVEL PYRAZOLO[1,5-a]PYRIMIDINE DERIVATIVES AS mTOR INHIBITORS |
| US8946216B2 (en) | 2010-09-01 | 2015-02-03 | Merck Sharp & Dohme Corp. | Indazole derivatives useful as ERK inhibitors |
| US9242981B2 (en) | 2010-09-16 | 2016-01-26 | Merck Sharp & Dohme Corp. | Fused pyrazole derivatives as novel ERK inhibitors |
| EP2632472B1 (en) | 2010-10-29 | 2017-12-13 | Sirna Therapeutics, Inc. | Rna interference mediated inhibition of gene expression using short interfering nucleic acids (sina) |
| US9351965B2 (en) | 2010-12-21 | 2016-05-31 | Merck Sharp & Dohme Corp. | Indazole derivatives useful as ERK inhibitors |
| IN2013MN02170A (en) | 2011-04-21 | 2015-06-12 | Piramal Entpr Ltd | |
| WO2013063214A1 (en) | 2011-10-27 | 2013-05-02 | Merck Sharp & Dohme Corp. | Novel compounds that are erk inhibitors |
| EP2844261B1 (en) | 2012-05-02 | 2018-10-17 | Sirna Therapeutics, Inc. | SHORT INTERFERING NUCLEIC ACID (siNA) COMPOSITIONS |
| WO2014052563A2 (en) | 2012-09-28 | 2014-04-03 | Merck Sharp & Dohme Corp. | Novel compounds that are erk inhibitors |
| MX363243B (en) | 2012-11-28 | 2019-03-14 | Merck Sharp & Dohme | Compositions and methods for treating cancer. |
| BR112015013611A2 (en) | 2012-12-20 | 2017-11-14 | Merck Sharp & Dohme | compound and pharmaceutical composition |
| EP2951180B1 (en) | 2013-01-30 | 2018-05-02 | Merck Sharp & Dohme Corp. | 2,6,7,8 substituted purines as hdm2 inhibitors |
| EP3041938A1 (en) | 2013-09-03 | 2016-07-13 | Moderna Therapeutics, Inc. | Circular polynucleotides |
| WO2019094311A1 (en) | 2017-11-08 | 2019-05-16 | Merck Sharp & Dohme Corp. | Prmt5 inhibitors |
| WO2020033284A1 (en) | 2018-08-07 | 2020-02-13 | Merck Sharp & Dohme Corp. | Prmt5 inhibitors |
| US20210277009A1 (en) | 2018-08-07 | 2021-09-09 | Merck Sharp & Dohme Corp. | Prmt5 inhibitors |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1990005525A1 (en) * | 1988-11-23 | 1990-05-31 | Pfizer Inc. | Quinuclidine derivatives as substance p antagonists |
| FR2654726B1 (en) * | 1989-11-23 | 1992-02-14 | Rhone Poulenc Sante | NEW ISOINDOLONE DERIVATIVES AND THEIR PREPARATION. |
| FR2654725B1 (en) * | 1989-11-23 | 1992-02-14 | Rhone Poulenc Sante | NEW ISOINDOLONE DERIVATIVES, THEIR PREPARATION AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THEM. |
| FR2676443B1 (en) * | 1991-05-17 | 1993-08-06 | Rhone Poulenc Rorer Sa | NOVEL PERHYDROISOINDOLE DERIVATIVES AND THEIR PREPARATION. |
-
1991
- 1991-05-17 FR FR9106035A patent/FR2676442B1/en not_active Expired - Fee Related
-
1992
- 1992-05-14 IL IL101866A patent/IL101866A0/en unknown
- 1992-05-15 DE DE69209290T patent/DE69209290T2/en not_active Expired - Fee Related
- 1992-05-15 CA CA002109298A patent/CA2109298A1/en not_active Abandoned
- 1992-05-15 HU HU9303249A patent/HUT67649A/en unknown
- 1992-05-15 EP EP92911474A patent/EP0586490B1/en not_active Expired - Lifetime
- 1992-05-15 JP JP4510462A patent/JPH06507627A/en active Pending
- 1992-05-15 ES ES92911474T patent/ES2085627T3/en not_active Expired - Lifetime
- 1992-05-15 TW TW081103795A patent/TW200459B/zh active
- 1992-05-15 DK DK92911474.2T patent/DK0586490T3/en active
- 1992-05-15 MX MX9202287A patent/MX9202287A/en unknown
- 1992-05-15 CZ CS932447A patent/CZ244793A3/en unknown
- 1992-05-15 US US08/146,143 patent/US5451601A/en not_active Expired - Fee Related
- 1992-05-15 NZ NZ242772A patent/NZ242772A/en unknown
- 1992-05-15 SK SK1267-93A patent/SK126793A3/en unknown
- 1992-05-15 EP EP92401329A patent/EP0514273A1/en active Pending
- 1992-05-15 ZA ZA923540A patent/ZA923540B/en unknown
- 1992-05-15 AU AU18836/92A patent/AU1883692A/en not_active Abandoned
- 1992-05-15 AT AT92911474T patent/ATE135687T1/en active
- 1992-05-15 WO PCT/FR1992/000429 patent/WO1992020653A1/en active IP Right Grant
- 1992-07-01 IE IE157892A patent/IE921578A1/en not_active Application Discontinuation
-
1993
- 1993-11-02 NO NO933964A patent/NO933964L/en unknown
- 1993-11-16 FI FI935071A patent/FI935071A0/en unknown
-
1996
- 1996-03-21 GR GR950403441T patent/GR3019386T3/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2676442B1 (en) | 1993-08-06 |
| FI935071A (en) | 1993-11-16 |
| DE69209290T2 (en) | 1996-10-31 |
| HUT67649A (en) | 1995-04-28 |
| ES2085627T3 (en) | 1996-06-01 |
| DK0586490T3 (en) | 1996-04-15 |
| DE69209290D1 (en) | 1996-04-25 |
| NO933964D0 (en) | 1993-11-02 |
| CZ244793A3 (en) | 1994-03-16 |
| US5451601A (en) | 1995-09-19 |
| FR2676442A1 (en) | 1992-11-20 |
| ATE135687T1 (en) | 1996-04-15 |
| TW200459B (en) | 1993-02-21 |
| SK126793A3 (en) | 1994-11-09 |
| NZ242772A (en) | 1994-04-27 |
| IL101866A0 (en) | 1992-12-30 |
| ZA923540B (en) | 1993-01-27 |
| IE921578A1 (en) | 1992-11-18 |
| NO933964L (en) | 1993-11-02 |
| JPH06507627A (en) | 1994-09-01 |
| GR3019386T3 (en) | 1996-06-30 |
| WO1992020653A1 (en) | 1992-11-26 |
| EP0514273A1 (en) | 1992-11-19 |
| CA2109298A1 (en) | 1992-11-18 |
| EP0586490B1 (en) | 1996-03-20 |
| HU9303249D0 (en) | 1994-03-28 |
| FI935071A0 (en) | 1993-11-16 |
| AU1883692A (en) | 1992-12-30 |
| EP0586490A1 (en) | 1994-03-16 |
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